766-99-4

134856-58-9

766-99-4

General procedure for the synthesis of 4-iodophenylacetylene from (4-iodophenylethynyl)trimethylsilane: To a solution of (4-iodophenylethynyl)trimethylsilane (5) (2.07 g, 6.23 mmol) in methanol (40 mL) was added K2CO3 (8.0 g, 57.9 mmol), and the reaction mixture was stirred for 48 hours. Upon completion of the reaction, the volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and H2O. The organic and aqueous layers were separated and the aqueous phase was re-extracted with ethyl acetate (2 x 20 mL). The organic layers were combined, washed sequentially with H2O and brine, dried with Na2SO4 and filtered. The solvent was removed in vacuum and the residue was crystallized from hexane at -20 °C (in two batches) to afford 1-ethynyl-4-iodobenzene (6) as a colorless solid (0.92 g, 64% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.66 (app d, J=8.6 Hz, 2H), 7.20 (app d, J=8.5 Hz, 2H), 1.54 (s, 1H).